Oakland Vacations from $524
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Your Oakland Vacation
From its cycling to its walking, there's tons to love about Oakland. Book a customized Oakland vacation package and get ready to fall for the delights of this neighborhood. When it's time to head out and explore, you'll find lots of big-name attractions nearby including Acrisure Stadium, University of Pittsburgh and PNC Park. Tick off one, two or all during your trip to Oakland. No matter your travel plans or budget, booking the ultimate Oakland vacation is simple with Expedia.
The Latest Oakland Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express & Suites Pittsburgh North Shore by IHG
North Shore
Save 100% on your flight
Price was $709, price is now $524 per person
$524
per person
May 1 - May 3
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Pittsburgh (PIT)
8.6/10 Excellent! (1,318 reviews)
Room was great, except view. View was the wall of the building next door.
Breakfast was great!
Reviewed on Feb 23, 2026
Red Roof Inn PLUS+ Pittsburgh East - Monroeville
Save 100% on your flight
Price was $865, price is now $569 per person
$569
per person
Apr 23 - Apr 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Pittsburgh (PIT)
6/10 (1,007 reviews)
somewhat-- make sure there is toilet paper in the room
Reviewed on Feb 9, 2026
Placemakr Downtown Pittsburgh at The Pennsylvanian
Downtown Pittsburgh
Save 100% on your flight
Price was $1,952, price is now $1,330 per person
$1,330
per person
Apr 23 - Apr 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Pittsburgh (PIT)
7.6/10 Good! (37 reviews)
Very friendly staff and clean room.
Reviewed on Feb 1, 2026
Where to stay in Oakland
Find the best Oakland areas and neighborhoods for the activities you enjoy most. Learn more about Oakland
Downtown Pittsburgh
2 out of top 10 points of interest in this area
4.5/5(2,251 area reviews)
Discover the urban downtown center, home to historic sites like Point State Park and the Cultural District. Enjoy diverse shopping options and easy access to public transportation, including the "T" light rail and bus networks.
Oakland Hotel Deals
Courtyard by Marriott Pittsburgh University Center
100 Lytton Avenue Pittsburgh PA
Fully refundableReserve now, pay when you stay
$130 nightly
The price is $148 total per night from Mar 24 to Mar 25
$148 total
Mar 24 - Mar 25
Total with taxes and fees
9/10 Wonderful! (620 reviews)
The rooms were great, but the breakfast at the hotel was very poor and expensive
Reviewed on Feb 23, 2026
Hotel Indigo Pittsburgh University-Oakland by IHG
329 Technology Drive Pittsburgh PA
Fully refundable
$119 nightly
The price is $136 total per night from Mar 1 to Mar 2
$136 total
Mar 1 - Mar 2
Total with taxes and fees
8.6/10 Excellent! (1,000 reviews)
Room was clean , staff was friendly! Absolutely wonderful stay .
Reviewed on Feb 23, 2026
The Oaklander Hotel, Autograph Collection
5130 Bigelow Boulevard Pittsburgh PA
Fully refundableReserve now, pay when you stay
$199 nightly
The price is $227 total per night from Mar 22 to Mar 23
$227 total
Mar 22 - Mar 23
Total with taxes and fees
9.2/10 Wonderful! (743 reviews)
Autograph hotels are my preferred choice hotel, but this one does not meet the expectations whatsoever. It was filthy and needs a deep clean. The base of the toilet had urine stains, There were yellow stains all over the walls of the bathroom. Mold in the shower. The Nespresso machine with filthy. ...
Reviewed on Feb 21, 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Discover the most popular places to visit in Oakland
University of Pittsburgh
Enjoy the collegiate vibe around University of Pittsburgh, a top college in Pittsburgh. Stroll along the riverfront or experience the acclaimed theater scene in this vibrant area.
Carnegie Museum of Natural History
From rare jaguars to geological marvels and ancient fossils, you’ll find it all at this Pittsburgh institution, one of the country’s largest natural history museums.
Carnegie Museum of Art
If you like your art with a modern twist, you’re in for a treat at this exceptional museum, which also features impressive furniture and architecture galleries.
Things to do
Pittsburgh Penguins Ice Hockey Game at PPG Paints Arena
$92
per adult
Pittsburgh Bar Hunt: Party Through Pittsburgh Bar Crawl
$13
per adult
Pittsburgh: Beauty of the Burgh Bike Tour
$59
per adult
94% of travellers recommend
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- University of Pittsburgh
- University of Pittsburgh Medical Center
- The Nationality Rooms
- Petersen Events Center
- Cathedral of Learning
- Soldiers and Sailors Memorial Hall and Museum
- Carnegie Museum of Natural History
- Heinz Memorial Chapel
- Carnegie Museum of Art
- Phipps Conservatory
- Schenley Park
- Carnegie Mellon University
- Hunt Institute for Botanical Documentation
- Pittsburgh Opera
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- Clemente Museum
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- Contemporary Craft
- Market Square
- Visit Pittsburgh
- South Side Vacations
- Ppg Paints Arena
- Temple Sinai
- Senator John Heinz Regional History Centre
- Duquesne University
- Walnut Street
- Western Pennsylvania Sports Museum
- Visit Shadyside
- Roberto Clemente Bridge
- Chatham University
- Visit Bloomfield
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.